As truckers navigate the challenges of 2026, both optimism and risk define the road ahead.
The HUB International Transportation Outlook found that 52% of transportation leaders are highly confident in their performance and profitability this year. Yet that optimism is tempered by vulnerability: 73% of companies also acknowledged they are underinsured against profit-threatening risks.
Freight volumes add a structural challenge. Shipments were down 6.9% year-over-year as of July 2025, marking the steepest drop since January and extending a multi-year downward trend.
Fleet performance, however, is shaped by more than miles driven or freight delivered.
Sixty-eight percent of U.S. fleet professionals say stress is negatively affecting driver performance, and 86% believe accident risk has increased in the past five years. Left unaddressed, driver pressures translate to higher claims, higher turnover and reduced productivity.
The reality is that in a high-cost, high-risk operating environment, new trucks and compliance alone will not deliver performance. Fleets that want to compete at the highest level must focus on benefits and leadership strategies that prioritize drivers and their on-the-road safety.
Compete for drivers with strategic benefits
The U.S. trucking sector continues to grapple with significant labor shortages, with projections estimating a 160,000 deficit by 2030. Retirements are accelerating while younger workers are slower to enter the field.
Fleets can gain ground in the talent market by:
- Differentiating benefits: Going beyond standard medical coverage with programs like mental health support, financial wellness resources, or ergonomic truck upgrades.
- Designing driver-specific policies: Offering flexibility in scheduling, consistent home time, and even family support services such as childcare assistance.
- Recognizing reliability: Celebrating everyday consistency and safe driving milestones builds loyalty as much as pay or bonuses.
Retaining skilled drivers reduces turnover costs and builds an experienced, stable workforce — factors that tend to lower risk and improve insurance terms.
Invest in health and wellness as a safety strategy
The health risks facing commercial drivers are multi-layered but interconnected. Long hours and sedentary schedules contribute to higher levels of cholesterol and rates of smoking, obesity and diabetes than the U.S. average. At the same time, the pressures of isolation and irregular schedules can drive elevated levels of stress, anxiety and depression.
These issues rarely exist in isolation: Fatigue worsens stress, and stress contributes to chronic health conditions. Together, they translate into more accidents, absenteeism and medical claims.
Fleets can address these issues with a tiered approach:
- Begin with awareness campaigns. Share resources on nutrition, proper rest and stress management to help drivers recognize risks early.
- Provide tools. Offer wellness apps, access to employee assistance programs, fitness resources designed for life on the road and ergonomic modifications to reduce strain.
- Implement systemic changes. Redesign schedules to reduce fatigue, create fair pay structures, train supervisors in mental health first aid, and establish policies that normalize conversations about health and wellness.
By addressing both physical and mental health together, fleets strengthen safety, reduce preventable incidents and show insurers that they are actively managing risk at its root.
Build a culture of safety to reduce risk
While 62% of companies have implemented enterprise-wide risk assessments — a signal that culture and leadership are being recognized as critical to controlling exposures — assessments alone don’t reduce losses. Daily practices do. A culture of safety empowers drivers and staff to share information, correct mistakes and prevent incidents before they escalate.
Fleets can put this into practice by:
- Building a debrief culture. Debriefs create space to capture lessons learned, celebrate wins and identify fixes before small errors become costly claims. Over time, this reduces repeat incidents and sharpens execution.
- Empowering functional leaders. Drivers, dispatchers and frontline staff often see risks before management does. Encouraging them to raise concerns helps prevent claims and reduces severity.
- Promoting psychological safety. Employees who feel free to speak up without fear of reprisal are more likely to report issues early. That transparency improves risk control and signals to underwriters that the fleet takes safety seriously.
These practices transform safety from a compliance checklist into a living culture, improving both driver engagement and insurability.
Turning benefits into business resilience
Freight demand remains uncertain, costs are rising and risk exposures are evolving faster than traditional approaches can keep up. Benefits, wellness programs and safety practices are often seen as add-ons, but in today’s reality, they are levers for long-term resilience.
The fleets that move first to integrate these strategies into daily operations will not only reduce claims and retain talent, but they will also position themselves to weather market cycles and secure more favorable insurance outcomes.
In an industry where margins are thin and volatility is high, that edge matters.
The question for fleet leaders isn’t whether to invest in drivers’ well-being and culture; it’s how quickly they can align those investments with the organization’s performance goals. The fleets that do so will set the standard for what high performance looks like in 2026 and beyond.
Dan Wilhelm, CIC, is the transportation practice leader for global insurance brokerage Hub International. He has more than 25 years of insurance experience, and a strong entrepreneurial background. He specializes in complex risk for all lines of coverage for middle market and large accounts related to automobile, construction, manufacturing, food processing, distribution and transportation. He is licensed in property and casualty as well as life and health. Dan helps develop cost-effective and comprehensive insurance programs for all areas of coverage.
